In application Ser. No. 417,963, filed Nov. 21, 1973, now U.S. Pat. No. 3,929,821, which is a continuation-in-part of application Ser. No. 319,299, filed Dec. 29, 1972, now abandoned, there are described novel benzene ring substituted benzimidazole-2-carbamate derivatives represented by the following formula: ##SPC2##
Where R is a lower alkyl group having 1 to 4 carbon atoms; R.sup.1 is --SOR.sup.2,--SO.sub.2 R.sup.2, --SCN, --SR.sup.5, --OR.sup.5 or M' (CH.sub.2).sub.n MR.sup.7 where M and M' are independently O, S, ##STR1## R.sup.7 is lower alkyl having 1 to 4 carbon atoms or aryl, and n is 1-4; R.sup.2 is a lower alkyl having from 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl, or lower alkynyl having 3 to 6 carbon atoms, or aralkyl or aryl; R.sup.5 is lower alkenyl, lower alkynyl or aralkyl; and the R.sup.1 substitution is at the 5(6)-position.
As stated therein, the term "lower alkyl" referred to both straight and branched chain alkyl groups having either a total of from 1 through 4 carbon atoms or from 1 through 6 carbon atoms, and thus included primary, secondary and tertiary alkyl groups. Typical lower alkyls included, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-amyl, n-hexyl and the like. The term "cycloalkyl" referred to cyclic hydrocarbon groups having from 3 to 7 carbon atoms such as, for example, cyclopropyl, cyclopentyl, cyclohexyl, and the like. The term "lower alkenyl" referred to an unsaturated hydrocarbon group having from 3 to 6 carbon atoms and a single carbon-carbon double bond, provided that the double bond was not on the .alpha.-carbon atom. Typical alkenyl groups included, for example, 2-propenyl, 2-butenyl, 3-butenyl, and the like. The term "lower alkynyl" referred to an unsaturated hydrocarbon group having from 3 to 6 carbon atoms, and a single carbon-carbon triple bond, provided also that the triple bond was not on the .alpha.-carbon atom. Typical alkynyl groups included, for example, 2-propynyl, 2-butenyl, 3-butynyl, and the like. It was stated that an alkyl, alkenyl or alkynyl group of the R.sup.1 moiety could be optionally substituted with one or more radicals, for example, thiocyanato; alkoxy, such as methoxy; aryl, such as phenyl; aroyl, such as benzoyl; hydroxy; cycloalkyl; halo; cyano; or nitro radicals. The term "alkoxy" referred to the group having the formula RO- wherein R is a lower alkyl as defined above. Typical alkoxy groups included, for example, methoxy, ethoxy, t-butoxy and the like. The term "halo" referred to iodo, bromo, chloro and fluoro groups. The term "aryl" referred to an aromatic hydrocarbon group, such as phenyl. The term "aralkyl" referred to an aryl substituted alkyl group, such as, for example, benzyl of phenethyl. The term "aroyl" referred to the group having the formula ##STR2## where R' is an aryl group. The aryl or aralkyl groups could be optionally substituted with one or more lower alkyl, alkoxy, halo, nitro, cyano, thiocyanato, isothiocyanato, trifluoromethyl, alkylthio, alkylsulfinyl, alkylsulfonyl, acyl or acylamino where the acyl portion has 1 to 6 carbon atoms, --SO.sub.2 NR.sup.3 R.sup.4 or --N(R.sup.3)SO.sub.2 R.sup.4 radicals; where R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms. The terms "alkylthio", "alkylsulfinyl", and "alkylsulfonyl" referred to those groups having the formula RS-, ##STR3## and ##STR4## respectively, where R is a lower alkyl (1-6C) as defined above. The term "acyl" referred to acyl groups derived from carboxylic acids having 1 through 6 carbon atoms such as acetyl, propionyl, butyryl, valeryl, isovaleryl, hexanoyl and the like.